92142-32-0

Usage

Uses

Used in Pharmaceutical Industry:
(-) ANATOXIN-A FUMARATE is used as a research compound for studying the effects of acetylcholine receptor-ion channel activation and blockade. Its agonistic properties make it a valuable tool in understanding the mechanisms of neuromuscular transmission and the development of drugs targeting these receptors.
Used in Neurological Research:
(-) ANATOXIN-A FUMARATE is used as a research tool in neurological research to investigate the role of acetylcholine receptors in various neurological disorders and diseases. Its ability to activate and block these receptors can provide insights into the development of potential therapeutic agents for conditions such as Alzheimer's disease, Parkinson's disease, and myasthenia gravis.
Used in Toxicological Studies:
(-) ANATOXIN-A FUMARATE is used in toxicological studies to evaluate the potential toxic effects of (-) ANATOXIN-A FUMARATE on various biological systems. Understanding its toxicological profile can help in the development of antidotes or countermeasures in cases of exposure to this toxin.

InChI:InChI=1/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3/t8-,10-/m0/s1

Upstream product

• 108585-39-3 2-acetyl-9-azabicyclo[4.2.1]non-2-ene-9-carboxylic acid methyl ester 
• 633294-91-4 (R)-5-(but-3-en-1-yl)pyrrolidin-2-one 
• 90741-53-0 t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate 
• 92998-50-0 (+/-)-2-acetyl-9-(tert-butoxycarbonyl)-9-azabicyclo<4.2.1.>non-2-ene 
• 70003-94-0 (1S,6S)-1-(9-Aza-bicyclo[4.2.1]non-2-yl)-ethanone 
• 108585-35-9 2-But-3-enyl-5-ethoxy-pyrrolidine-1-carboxylic acid methyl ester 
• 108585-34-8 2-But-3-enyl-5-oxo-pyrrolidine-1-carboxylic acid methyl ester 
• 101347-86-8 (racemic)-5-(2'-butenyl)-2-pyrrolidinone 
• 111723-01-4 (1R,6S)-4-Chloro-9-aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 2-ethyl ester 9-methyl ester 
• 111723-02-5 (1R,6R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 2-ethyl ester 9-methyl ester 
• 111723-03-6 (1R,6R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-methyl ester 
• 111722-98-6 1-ethoxy-1-trimethylsiloxy-1,4-pentadiene 
• 85514-42-7 anatoxin-a 

Downstream Products

• 64314-16-5 (+/-)-anatoxin-a 
• 90741-54-1 (R)-1-((1S,6S)-2-Acetyl-9-aza-bicyclo[4.2.1]non-2-en-9-yl)-3,3,3-trifluoro-2-methoxy-2-phenyl-propan-1-one 
• 90741-53-0 t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate 

Relevant academic research and scientific papers

Investigation of a unified strategy for the synthesis of anatoxin analogues: Scope and limitations

Syntheses of the potent neurotoxins and biochemical probes anatoxin-a and homoanatoxin and several analogues by a combined two-directional synthesis-tandem reaction strategy are presented. Key steps include an oxidative desymmetrisation and a tandem Micha

Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame

This paper describes the total synthesis of the naturally occurring alkaloids pinnamine (1) and anatoxin-a (2) from a common enantiomerically pure intermediate (7) easily available from pyroglutamic acid. The synthesis of enantiopure pinnamine proceeded in 10 steps and 4.8% overall yield, and the route was flexible enough to allow stereocontrolled access to a non-natural congener (5-epi-pinnamine) of the natural product. Intramolecular reaction of an N-acyl iminium ion was a key step in the synthesis of both pinnamine and anatoxin-a. However, in stark contrast to literature precedent, complete racemization was observed during the reaction of the N-acyliminium ion leading to the latter alkaloid.

Synthesis of (±)-anatoxin-α and analogues

A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-α and its analogues is described, which uses a β-lactam ring opening-transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The synthesis involves a cycloaddition of chlorosulfonyl isocyanate with cyclooctadiene followed by Boc protection of the resulting β-lactam. Reaction of the β- lactam with a variety of nucleophiles, followed by selenium-mediated cyclisation and oxidation gave the skeleton of anatoxin-α bearing various sidechains. The approach offers a flexible entry to useful quantities of anatoxin-α and its analogues.

Tandem reactions of anions: A short and efficient route to ±anatoxin-a

A new route to anatoxin-a (1) is reported which involves an anionically induced small ring opening/ring closure/ring opening cascade. The azabicyclo [4.2.1]nonane ring system of anatoxin-α is hence formed in one synthetic operation.

Efficient new syntheses of (+)and (-)-anatoxin-a. Revised configuration of resolved 9-methyl-9-azabicyclo[4.2.1]nonan-2-one

The bicyclic ketone 2, as either enantiomer, was converted in high yield to the glycidonitrile 4 by successive base-catalysed condensation with 2-chloropropionitrile and N-dealkylation. Opening of the epoxide followed by elimination of HCl from the resulting α-chloroketone gave the enone 7 which was converted to anatoxin-a 1 by mild acidolysis. Maintenance of chiral homogeneity from both (+)- and (-)2 was demonstrated by diastereomeric amide formation from (+)- and (-)-1. However, the prior correlation of (+)- 2 with (+)- 1 was found to be incorrect; in fact (-)- 2 gives (+)- 1.

A concise asymmetric synthesis of (-)-anatoxin-a using an enantioselective enolisation strategy

The unnatural enantiomer of anatoxin-a is prepared in enantiomerically pure form by a concise route involving enantioselective enolisation of a tropinone derivative by a chiral lithium amide base as the key step.

A New Method of Formation of 9-Azabicyclononane Skeleton and Its Application to Synthesis of (+/-)-Anatoxin a

9-Azabicyclo-nonane skeleton was formed in one step by Lewis acid promoted reaction between 1-methoxycarbonyl-2,5-dimethoxypyrrolidine and 1-ethoxy-1-trimethylsiloxy-1,4-pentadiene, and it was converted to (+/-)-anatoxin a.